Kapugedera made his first-class debut in a match for Sri Lanka A and in domestic cricket, he plays for Colombo Cricket Club.
An aggressive right-handed batsman, Kapugedera got his first taste of international cricket when he made his One Day International debut against Australia in Perth in 2006.He was the first Sri Lankan national ODI cricketer to emerge from his school Dharmaraja College in Kandy, which is one of the leading schools in the island.He made his Test cricket debut in the first Test against England at Lord's Cricket Ground in London, in May 2006, in which he made a first ball duck in the first innings. A stylish and classical player, he is also known for his big hitting and his innings of 38 runs from 21 balls, inclusive of 2 fours and 3 sixes, in the first final of the VB Series held in 2006. This innings bolstered Sri Lanka's total and ensured that Australia lost their first home final in 9 years.
Although Kapugedera showed huge potential in both one day and Test cricket, with some mature innings, his overall inconsistency lead to him being dropped from both teams. However, after the 2007 World Cup he began to stabilise his position in the one day team, and in 2008 some good performances cemented his position in the number 4 position. This included a 95 against West Indies when Sri Lanka were in trouble, and in the Asia Cup.
His inconsistency during 2009 has proved costly, with more young players coming through to challenge for his place in the team. Chennai Super Kings put him on sale for the 2009 Indian Premier League, but no team came forward to bid for him despite the very low starting price.